Both the typical yellow form of Freesia leichtlinii (Dune Freesia) and the white form (previously known

as Freesia alba) are important in the origin of modern freesia cultivars.

Scentsational freesias
by John Manning and Roman Kaiser

Chemical analysis of the fragrance of freesias supports the division of the genus Freesia into two groups based on DNA and bract texture

or city dwellers around the world, the appearance of freesias in florists shops and in the barrows of flower sellers on street corners is the urban equivalent of the unfurling of spring wildflowers in fields and woodlands. Unlike many of their rural cousins, however, freesias pour forth a strong, sweet fragrance from their trumpet-shaped flowers, sounding a brilliant olfactory fanfare to dispel the dreary northern winter. Their bright sprays of blossom burst onto streets with the lan of a cancan chorus line, the ruffled flowers dancing down each stem in a perfectly choreographed row, petals swirling around dainty, creamy stamens vivacious and irresistible as the grisettes of Maxims. Modern freesia cultivars, puffed up by polyploidy, are essentially the product of the ingenuity and application of late-Victorian and Edwardian breeders in Europe. The wild species from which their stocks were originally drawn are endemic to the south-western Cape but are barely known, even in their native land. Botanists today recognize 16 species of Freesia, one of them so recently recognized that it has yet to be formally named. All but four of the known wild species are endemic to Namaqualand and the southwestern Cape, with the greatest concentration in the Worcester-Little Karoo and adjacent littoral, in the Overberg and the southern Cape. Known colloquially as flissies from their flask-shaped flowers arranged in perky, arched spikes, most species exude a heady, violet-like fragrance during the day.
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Tentative beginnings The first freesias found their way to Europe in the mid Seventeenth Century at a time of rising interest in Cape plants. Bulbs and succulents were among the plants that most readily survived the rigours of the long sea voyages from the Cape to the ports of Europe, and the first two Freesia species known to science were described from plants that had been established in cultivation in The Netherlands some time prior to 1768. They were given names that alluded to some notable characteristic, aptly in one case the striking fragrance for which the genus would later become famous. In naming F. caryophyllacea, the Carnation-scented Freesia, however, the Dutch botanist Nicolaas Burman reveals a deplorable knowledge of bouquet since no species of Freesia produces oil of cloves, the primary component of the smell of wild carnations. In keeping with botanical conventions of his day, Burman placed his two new species in the genus Gladiolus on account of their two-lipped, trumpet-shaped flowers. Freesia itself was only established as a separate genus a century later, in 1866, by the German botanist, F.W. Klatt, who is honoured in another botanical curiosity from the Cape, the shrubby iris Klattia. At this time the name Freesia was applied only to those species with the characteristic funnel-shaped flowers that are familiar to us from the cultivated forms, but three decades later Klatt expanded his conception of the genus to include a few species with narrowly tubular, mostly unscented flowers,

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notably the Forest Painted-petals, F. grandiflora and F. laxa, both with brilliant scarlet, salver-shaped blooms. It is this circumscription that we follow today. By the end of the nineteenth century, just over half of the currently accepted species of Freesia were known to science, all of them collected and described by European botanists. The establishment of a botany department at the South African College (later the University of Cape Town) in 1903 and of Kirstenbosch Gardens (now Kirstenbosch National Botanical Garden) ten years later, marked the beginning of indigenous scientific study in South Africa, leading directly to the discovery and description of four more species of Freesia in the first decades of the Twentieth Century. Here the total remained until the opening years of this century, during which another three highly localized species will have been named, bringing the number of species of Freesia to its current total. These 16 names are not, however, the only ones to appear in the botanical and horticultural literature as many Freesia species were known under more than one name to different botanists. Early botanical accounts of Freesia bear little resemblance to our current understanding of the genus, and this confused legacy is especially pernicious in attempts at understanding the early history of the cultivars. The first attempt at a comprehensive treatment of Freesia in its classic sense was that of the late-Victorian British botanist, J.G. Baker, who recognized just the single species Freesia refracta, which he subdivided into three varieties that we recognize today as three distinct species. Bakers understanding of the genus was derived primarily from information supplied by the amateur horticulturist, M. Foster, Professor of Physiology at Cambridge, but despite their best efforts, the exact application of some of the other names current at this time remained uncertain. The misuse of the name F. refracta in the horticultural literature for forms of F. corymbosa and F. leichtlnii stems from this time true F. refracta was never used in Freesia breeding. The naming of several new species of Freesia in the early decades of the Twentieth Century

by the South African botanist H.M.L. (Louisa) Bolus stimulated the first modern treatment of Freesia by the English botanist, N.E. Brown, who distinguished no less than nineteen species, many of them now understood to be nothing more than minor colour and leaf variants. Brown was, however, the first to recognize the important difference in the texture of the floral bracts that has turned out to be so pivotal in our modern classification of the genus. Browns plethora of poorly defined species was consolidated in the last decades of the Twentieth Century by Peter Goldblatt, who also succeeded in pinning down several of the early names that had confused earlier botanists. The modern synthesis By now it was accepted that freesias came in two very different floral forms but it was not clear exactly how these two types related to one another. The first attempt at an evolutionary analysis focused on floral characteristics, and it confirmed the prevailing idea that the classic, funnel-flowered species comprised a discrete lineage of closely related species. This contrasted sharply with the situation among the tubularflowered species, which fell into three different groups, indicating a far less intimate relationship among them. These results suggested that earlier botanical practice, which grouped the four tubular-flowered species together in the genus Anomatheca, required serious reconsideration. The development of DNA-based techniques for studying relationships among organisms offered a chance to resolve these two conflicting ideas. Carried out in conjunction with Dr Flix Forest at Kew, the picture that emerges is fascinating and provocative. Like the morphological analysis, the DNA analysis places the tubularflowered species in three separate lineages but rather than forming a loose alliance set apart from the trumpet-flowered species, the tubularflowered plants appear to be closely entangled among the classic freesia flowered species. In fact, the primary division among species of Freesia coincides not with flower shape at all but exactly with the difference in

LEFT: Freesia speciosa, a rare species from the western Little Karoo, has the largest flowers of all wild freesias. RIGHT: Freesia grandiflora, a widespread species of tropical and subtropical woodland, with unscented, scarlet flowers, was previously placed in the genus Anomatheca on account of its slender floral tube. Photos: J. Manning.
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A.

K52936 30m CP-Wax 52CB,1l on column

RT: 2.30 - 50.00
100 95

Freesia leichtlinii, Kirstenbosch, 28.7.05, 9.00-15.00

-Terpineol

NL: 1.14E9 m/z= 33-350

B.

K69618 30m CP-Wax 52CB, 1.2l on column RT: 2.30 - 50.00

100 95 90

Freesia x hybrida yellow,18.4.09, 11.00-14.00

Linalool
NL: 7.27E8 m/z= 33-350

-Ionone

85 80

(E)-Ocimene

90

85

Relative Abundance

75 70 65 60 55

OH

Relative Abundance

80 75 70 65

2-Methylbutyraldoxime (E+Z)

Eucalyptol

-Terpineol -Selinene

50 45

OH

55 50 45

2-Methylbutyraldoxime

OH

60

Dihydro- -ionone

Caryophyllene

Limonene

Linalool

-Selinene

30 25 20 15 10 5 0 4

30 25 20 15 10 5

10

12

14

16

18

20

22

24

26

28

30

32

34

36

38

40

42

44

46

48

50

Time (min)

10

12

14

16

18

20

22

24

Time (min)

26

28

30

32

34

-Ionone
36 38

35

Eucalyptol

35

(E)-Ocimene

40

40

Dihydro- -ionone

Limonene

Caryophyllene

40

42

44

46

48

50

K63055 30m CP-Wax 52CB, 2 l on column

RT: 2.30 - 50.00
100 95 90 85 80
OH

Freesia corymbosa "armstrongii", 27.9.07, 11.00-16.00

Linalool
NL: 1.37E9 m/z= 33-350

K7704 30m CP-Wax 52CB, 1ul on column RT: 2.30 - 50.00

100 95 90

Freesia x hybrida white, 18.7.06, 9.40-13.40

Linalool 2-Methyl-2-vinyltetrahydrofuran-5-ol
NL:1.57E9 m/z= 33-350

2-Methyl-2-vinyltetrahydrofuran-5-one

2,6-Dimethylocta-3,7-dien-2,6-diol

2-Methyl-2-vinyltetrahydrofuran-5-ol

2,6-Dimethylocta-3,7-dien-2,6-diol

2,6-Dimethylocta-1,7-dien-3,6-diol

OH

85

Relative Abundance

60 55 50 45 40 35 30 25 20 15 10 5 0 4 6 8
O OH

OH

60 55

2-Methylbutyraldoxime

65

cis-Linalool oxide (furanoid)

70

trans-Linalool oxide (furanoid)

70 65

cis-Linalool oxide (furanoid)

75

OH

OH

75

trans-Linalool oxide (furanoid)

Relative Abundance

80

OH

OH

Tridecan-2-one

45 40 35 30 25 20 15 10 5

Eucalyptol

Limonene

(E)-Ocimene

50

10

12

14

16

18

20

22

24

26

28

30

32

34

36

38

40

42

44

46

48

50

Time (min)

10

12

14

16

18

20

22

24

Time (min)

26

28

30

32

34

36

38

40

42

44

2,6-Dimethylocta-1,7-dien-3,6-diol
46 48

-Terpineol

-Ionone

50

Gas chromatograms of selected Freesia species and cultivars. Individual peaks represent different chemical compounds, and the size of each peak is proportional to the relative concentration of that chemical. A The scent of F. leichtlinii is characterized by the presence, among other compounds, of high concentrations of -terpineol and -ionone as well as smaller amounts of three other diagnostic chemicals (Dihydro--ionone, 2-methylbutyraldoxime (E+Z) and -selinene), all highlighted in red. These particular compounds are absent from the scent of F. corymbosa, which is recognizable by the presence of trace amounts of four unusual chemicals derived from the more common, dominant constituent, linalool (2-methyl-2-vinyltetrahydrofuran-5-ol, 2,6-dimethylocta-3,7-dien-2,6-diol and 2,6-dimethylocta-1,7-dien-3,6-diol), all highlighted in blue. B White-flowered commercial Freesia cultivars betray their mixed parentage by combining the diagnostic fragrance markers of both F. leichtlini (highlighted in red) and especially F. corymbosa (highlighted in blue), whereas yellow-flowered cultivars approach pure Freesia leichtlinii in their fragrance. the texture of the floral bracts that had first been pointed out by Brown in 1935. On the one hand we have those species with firm-textured, green bracts, and on the other those with thinner, more membranous or even papery bracts. Both groups are dominated by species with funnelshaped flowers but each also contains one or more tubular-flowered species. This coincidence between DNA and bract type is reflected in our decision to recognize these two groups as subgenera. A cultivated past The history of modern freesia cultivars goes back to the late Nineteenth Century, with the introduction into cultivation of yellow- and whiteflowered forms of F. leichtlinii (the latter under the name F. alba). Selection from this material gave a range of white and yellow forms that enjoyed some popularity but it was the introduction of pink- and deep yellow-flowered forms of F. corymbosa (known respectively as F. armstrongii and F. aurea) in the closing years of the century that provided the real stimulus to freesia breeding. By the end of the first decade of the Twentieth Century the Dutch nursery firm of Van Tubergen had produced a range of tall freesias in a variety of colours including blue, mauve, shades of rose, yellow and white, and the first polyploid, Freesia Buttercup, made its appearance in 1911. Today most registered cultivars are polyploid, with diploid strains important mainly in areas where plants are grown every season from seed. Breeding of Freesia continues today with the resultant varieties, including double-flowered types, bearing less and less resemblance to the wild species from which their stock originally stemmed. The cultivars range from 1030 cm in height, in habit from neat and tufted to tall and graceful, in inflorescence from short and semi-erect to long, sparsely branched and horizontal, and producing scarcely to strongly fragrant flowers in almost every conceivable colour. Almost shockingly, however, no additional genotypes appear to have been introduced into the mix since those first crosses were made in the late Nineteenth Century, and all commercial freesias are essentially derived from repeated crossings of
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colour forms of just two wild species, F. corymbosa and F. leichtlinii. This is an almost incredible neglect of the potential that exists among the wild species for the addition of new flower shapes and other characteristics. Although freesias are famous for their fragrant flowers, typically but inadequately described in horticultural literature as sweet-smelling, very few cultivars have been developed primarily for their fragrance. Indeed, many commercial varieties have lost their scent during the breeding and selection processes, a cause for special concern among Chinese and Japanese growers. The favoured colours by far in both Holland and Japan are yellow, followed by white, and it is probably no coincidence that these colours are typically the most fragrant. Scenting success The division of Freesia into two groups based on DNA and bract texture has received spectacular support from our chemical analysis of floral fragrance in the genus. The scent in freesia flowers emanates primarily from the bright yellow or orange patches that decorate the lower lip of the flowers like smears of turmeric. Scented members of the group with delicate bracts, such as F. corymbosa, produce floral fragrances dominated either by the chemicals linalool (which has an attractive floral-woody smell) or nerol (fresh and rose-like with citrus undertones). Members of the group with leathery bracts, which includes F. caryophyllacea and F. leichtlini, are chemically more diverse, with scents that are dominated by nerol or -terpineol (sweet-floral with pine-needle undertones) but with the signal addition of the chemicals -ionone and dihydro--ionone (green-woody, fruity and very floral with a distinct freesia smell). The ionones, which are extremely potent with very low odour thresholds to the human nose, have found an enormous appreciation in perfumery during the past three decades and many of the famous fragrances contain high amounts of them, often in ratios similar to those found in nature. Relatively widespread among flowering plants, ionones have the curious characteristic that they are invisible to around 10% of humans who are unable to detect their odour through a genetic peculiarity. As

a result, people who cannot smell ionones will perceive the scent of flowers containing these chemicals in their fragrance spectrum quite differently from those fortunate enough to have active ionone receptors. A new beginning Our identification of ionone-negative and ionone-positive groups in the genus raises the exciting possibly of developing distinct fragrance-lineages in Freesia. The very early crossing of F. leichtlinii with F. corymbosa effectively removed this potential from current breeding programmes by unwittingly blending the two fragrance-groups. The new understanding of relationships among the species that was provided by DNA analysis opens up the opportunity for selective breeding within each of the two fragrance-groups to derive fragrance-cultivars that can only enhance our enjoyment of this wonderful genus. It is most unfortunate, for instance, that true F. refracta has never figured in the parentage of commercial cultivars as it has a rich, roselike scent stemming from the chemicals nerol, geraniol and citronellol. These rosy-floral and citrus-related scent constituents harmonize exquisitely with the fragrance of the existing cultivars. Another great mystery is why F. caryophyllacea, an attractive and relatively common species that was among the very first to be grown in Europe, has never been involved in breeding programmes. It offers ravishing rosy-floral fragrance notes via geraniol and nerol and their derivatives. Floral scents, elusive and evocative, add a final touch of glamour to the beauty of many of our wildflowers but they are a sadly underappreciated feature that richly rewards closer attention.

THE AuTHORS Dr John Manning is a Senior Specialist Scientist at the Compton Herbarium, South African National Biodiversity Institute, Kirstenbosch. Dr Roman Kaiser is a chemist at the Givaudan fragrances and flavours company in Switzerland.
WHAT DOES THAT MEAN? Diploid Two of each type of chromosome Genotype The genetic make-up of an organism as opposed to its physical characteristics Littoral Of or on the seashore Morphological Shape and form or physical characteristics of an organism Polyploidy Having more than the usual number of chromosomes

TOP: Freesia fucata, a rare species from near Villiersdorp, has the highly fragrant, funnel-shaped flowers that are characteristic of the genus. The scent in freesia flowers emanates primarily from the bright yellow patches that decorate the lower lip of the flowers like smears of turmeric. ABOVE: True Freesia refracta was never used in the breeding of freesia cultivars and references to it in the early horticultural literature actually apply to F. corymbosa and F. leichtlinii. Photos: J. Manning.
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